WO2016082999A1 - Agents de coloration de fibres kératiniques, contenant au moins un colorant azoïque dicationique dimère et au moins un tensioactif non ionique - Google Patents

Agents de coloration de fibres kératiniques, contenant au moins un colorant azoïque dicationique dimère et au moins un tensioactif non ionique Download PDF

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Publication number
WO2016082999A1
WO2016082999A1 PCT/EP2015/072774 EP2015072774W WO2016082999A1 WO 2016082999 A1 WO2016082999 A1 WO 2016082999A1 EP 2015072774 W EP2015072774 W EP 2015072774W WO 2016082999 A1 WO2016082999 A1 WO 2016082999A1
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Prior art keywords
phenyl
ium
ethyl
amino
methyl
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PCT/EP2015/072774
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German (de)
English (en)
Inventor
Antje Gebert-Schwarzwälder
Melanie Moch
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Henkel Ag & Co. Kgaa
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Priority to EP15771640.8A priority Critical patent/EP3223787B1/fr
Priority to US15/528,539 priority patent/US10226648B2/en
Publication of WO2016082999A1 publication Critical patent/WO2016082999A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/20—Thiazoles or hydrogenated thiazoles

Definitions

  • compositions for coloring keratinic fibers, in particular human hair which comprise (a) at least one dimeric dicationic azo dye of a specific formula (I) in combination with (b) at least one nonionic surfactant.
  • nonionic surfactants (b) can increase the color intensity of cationic azo dyes, in particular of the specific azo dyes of the formula (I).
  • a further subject of the present invention is therefore the use of nonionic surfactants (b) for improving the color absorption capacity of cationic azo dyes, in particular the special azo dyes of the formula (I), on keratinic fibers.
  • oxidation dyes For the dyeing of keratinic fibers, either direct dyes or oxidation dyes are generally used. Although intensive dyeings with good fastness properties can be obtained with oxidation dyes, the development of the color is generally carried out under the influence of oxidizing agents such. H2O2, which in some cases can result in damage to the fiber. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors may have a sensitizing effect on persons with sensitive skin. Direct dyes are applied under gentler conditions. Their disadvantage lies in the fact that the dyeings often have only insufficient fastness properties.
  • the expert uses substantive dyes of different classes of dyes.
  • the direct dyes known from the prior art include, for example, the class of nitro dyes, the anthraquinone dyes, the azo dyes, the triarylmethane dyes or the methine dyes. All of these classes of dyes should meet a specific requirement profile for use in the cosmetics sector. Thus, direct dyes should provide an intensive dyeing result and have the best possible fastness properties. Due to environmental influences, the color result obtained with substantive dyes should be influenced as little as possible, ie the dyes should have, for example, a good wash fastness, light fastness and rub fastness.
  • the keratinic fibers may be exposed to after the dyeing process (such as perms) should change the color result as little as possible.
  • the substantive dyes should if possible also be compatible with the oxidizing agents commonly used in the bleaching process (such as hydrogen peroxide and / or persulfates).
  • cationic azo dyes As a class of dyes with an outstanding requirement profile, cationic azo dyes have been found. Azo dyes are generally characterized by a high stability. In addition, cationic azo dyes, because of their positive charge, have a high affinity for keratinic fiber which, depending on their degree of damage, may be more or less negatively charged.
  • keratinic fibers are to be lightened or bleached oxidatively
  • substantive dyes can also be used in combination with oxidizing agents.
  • aqueous hydrogen peroxide solutions are usually applied to the keratin fibers, either alone or in combination with other oxidizing agents, such as persulfate salts, acting as bleach activators.
  • oxidizing agents such as persulfate salts
  • the pH is usually between 9 and 10.5.
  • the melanins are located in the cortex of the hair fiber and can be classified into two pigment classes. Eumelanins are the first brownish-black pigment class, while the reddish, sulfur-rich pigments are called pheomelanins.
  • the phae and eumelanins are not always uniformly decolorized.
  • the degradation of the melanins can be only partially or incompletely, so that after bleaching remains a residual proportion of the coloring pigments in the hair.
  • the residual content of melanins remaining in the hair after the oxidative process leads to a yellowish to reddish shift in shade. Therefore, especially when bleaching darker hair, there is a color shift towards warm (reddish) tones.
  • Basic Orange 31 (alternative name: 2 - [(4-aminophenyl) azo] -1,3-dimethyl-1H-imidazolium chlorides, CAS No. 97404-02, which are well-known from the prior art are cationic azo dyes 9) and Basic Red 51 (alternative name: 2 - [((4-dimethylamino) phenyl) azo] -1,3-dimethyl-1H-imidazolium chloride, CAS No. 77061-58-6).
  • the blue dyes contained in the funds should also be particularly well compatible with the cationic azo dyes Basic Orange 31 and Basic Red 51.
  • a first object of the present invention is an agent for dyeing keratinic fibers, in particular human hair, contained in a cosmetic carrier
  • R 1, R 4 independently of one another are a C 1 -C 6 -alkyl group, a C 2 -C 6 -alkenyl group, a hydroxy-C 2 -C 6 -alkyl group, a cyano-C 1 -C 6 -alkyl group, a halogeno-C 1 -C 6 -alkyl group, a Aryl-C 1 -C 6 -alkyl group, a heteroaryl-C 1 -C 6 -alkyl group, an aryl group or a heteroaryl group, R 2, R 3 independently of one another represent a hydrogen atom, a C 1 -C 6 -alkyl group, a C 2 -C 6 -alkenyl group, a hydroxy-C 2 -C 6 -alkyl group, a cyano-C 1 -C 6 -alkyl group, a halogeno-C 1 -C 6 -alkyl group, an aryl
  • R5, R6, R7, R8 independently represent a hydrogen atom, a Ci-C6-alkyl group, a
  • Halogen atom from the group consisting of chlorine, bromine, fluorine or iodine, or represents a C 1 -C 6 -alkoxy group
  • X1, X2 independently of one another represent a physiologically tolerable anion, preferably from the group chloride, bromide, iodide, methylsulfate, methylsulfonate, p-toluenesulfonate, acetate, hydrogensulfate, V 2 sulfate or V 2 tetrachlorozincate,
  • Q is a group of the formula (II), (III), (IV) or (V),
  • n is an integer from 3 to 6
  • R9 represents a hydrogen atom, a Ci-C6-alkyl group, a C2-C6-
  • Alkenyl group or represents a hydroxy-C 2 -C 6 -alkyl group
  • Keratinic fibers, keratin-containing fibers or keratin fibers are understood to mean furs, wool, feathers and, in particular, human hair.
  • compositions according to the invention are primarily suitable for whitening keratin fibers, in principle there is nothing to prevent their use in other fields as well.
  • coloring of keratin fibers used according to the invention encompasses any form of color change of the fibers, including in particular the terms tinting, bleaching, matting, oxidative dyeing, semi-permanent dyeing, permanent dyeing and temporary Staining included color changes.
  • Explicitly encompassed according to the invention are color changes which have a lighter color result in comparison to the starting color, for example coloring bleaching operations.
  • the term "matting of keratin fibers" is understood to mean the counteracting of undesired nuance shifts which occur in the case of oxidative color changes of keratin fibers, in particular bleaching operations or bleaching processes.
  • the aim of matting is to weaken the orange to reddish color impression caused by incomplete bleaching
  • the active ingredients used in matting can be applied after bleaching or bleaching the keratin fibers, but it is also possible to combine the active ingredients used for the matting in a one-step process
  • active substances suitable for matting substantive dyes, either alone or in the dye mixture, may be applied to the keratin fibers using the appropriate bleaching agent or bleach properties are used.
  • direct dyes for matting in combination with oxidation dye precursors (developers and couplers).
  • the agents according to the invention contain the substantive dyes of the formula (I) in a cosmetic vehicle.
  • This cosmetic carrier is preferably aqueous, alcoholic or aqueous-alcoholic.
  • such carriers are for example creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • a powdery or tablet-like formulation This is then mixed before use in an aqueous solvent or with organic solvents or with mixtures of water and organic solvents to obtain the application mixture.
  • an aqueous carrier contains at least 40% by weight, in particular at least 50% by weight, of water.
  • aqueous-alcoholic carriers are to be understood as meaning water-containing compositions containing from 3 to 70% by weight of a C 1 -C 4 -alcohol, in particular ethanol or isopropanol.
  • the compositions according to the invention may additionally contain other organic solvents, for example 4-methoxybutanol, ethyl diglycol, 1,2-propylene glycol, n-propanol, n-butanol, n-butylene glycol, glycerol, diethylene glycol monoethyl ether and diethylene glycol mono-n-butyl ether, contain. Preference is given to all water-soluble organic solvents.
  • Preferred agents according to the invention are characterized in that they additionally comprise a non-aqueous solvent, preferred agents according to the invention containing the solvent in a concentration of 0.1 to 30% by weight, preferably in a concentration of 1 to 20% by weight, very particularly preferably in a concentration of 2 to 10 wt .-%, each based on the agent.
  • the agents according to the invention contain at least one substantive dye of the formula (I).
  • R 1 to R 9 of the compounds of the formula (I) are described below by way of example:
  • Examples of a C 1 -C 6 -alkyl group are the groups methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl, n- Pentyl and n-hexyl.
  • Propyl, ethyl and methyl are preferred alkyl radicals.
  • Examples of a C2-C6 alkenyl group are vinyl, allyl, but-2-enyl, but-3-enyl and isobutenyl, preferred C2-C6 alkenyl radicals are vinyl and allyl.
  • Preferred examples of a hydroxy-C 1 -C 6 -alkyl group include hydroxymethyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 5-hydroxypentyl and 6-hydroxyhexyl; a 2-hydroxyethyl group is particularly preferred.
  • Preferred examples of cyano-C 1 -C 6 -alkyl groups are the cyano methyl group, the 2-cyanoethyl group and the 3-cyanopropyl group.
  • Halogen-C 1 -C 6 -alkyl groups which are preferred according to the invention are the chloromethyl group, the bromomethyl group, the fluoromethyl group, the 2-chloroethyl group, the 2-bromoethyl group, the 2-fluoromethyl group, the 2-chloropropyl group, the 2-bromopropyl group, the 2-fluorophenyl group 3-chloropropyl group, the 3-bromopropyl group and the 3-fluoropropyl group.
  • Preferred examples of aryl-C 1 -C 6 -alkyl groups are benzyl, 1-phenethyl and 2-phenylethyl.
  • heteroaryl-C 1 -C 6 -alkyl groups are the imidazol-1-ylmethyl group, the imidazol-2-ylmethyl group, the imidazol-4-ylmethyl group, the pyridin-2-yl group, the pyridin-3-yl group and the pyridine-4-yl group. ylmethyl devis be called.
  • Aryl groups preferred according to the invention are the phenyl group and the naphthyl group.
  • heteroaryl group examples include the pyridin-2-yl group, the pyridin-3-yl group, the pyridin-4-yl group, the imidazol-1-yl group, the imidazol-2-yl group and the imidazol-4-yl group.
  • Halogen atoms are selected from the group chlorine, bromine, fluorine and / or iodine, in which case chlorine and bromine are particularly preferred.
  • Exemplary of a C1-C6 alkoxy group, the methoxy, the ethoxy and the propoxy group can be mentioned.
  • the compounds of general formula (I) carry the radicals R1 and R4; Here R1 and R4 may be the same or different. Preferably, the radicals R1 and R4 are the same. Preferably, R 1 and R 4 independently of one another represent a C 1 -C 6 -alkyl group or a C 2 -C 6 -alkenyl group. More preferably, R 1 and R 4 independently of one another are a C 1 -C 6 -alkyl group, in particular a methyl group or an ethyl group.
  • the compounds of general formula (I) carry the radicals R2 and R3;
  • R2 and R3 may be the same or different.
  • the radicals R2 and R3 are the same.
  • R 2 and R 3 independently of one another represent a hydrogen atom, a C 1 -C 6 -alkyl group or a C 2 -C 6 -alkenyl group.
  • R 2 and R 3 independently of one another represent a hydrogen atom or a C 1 -C 6 -alkyl group.
  • R 2 and R 3 independently of one another represent a hydrogen atom, a methyl group or an ethyl group.
  • the compounds of the general formula (I) carry the radicals R5, R6, R7 and R8;
  • the radicals R5 to R8 may be the same or different.
  • the radicals R5, R6, R7 and R8 independently of one another represent a hydrogen atom, a halogen atom or a C 1 -C 6 -alkoxy group.
  • the radicals R5, R6, R7, and R8 are all a hydrogen atom.
  • an agent according to the invention is characterized in that it contains (a) at least one substantive dye of the general formula (I) in which
  • R 1, R 4 independently of one another represent a C 1 -C 6 -alkyl group
  • R 2, R 3 independently of one another represent a hydrogen atom or a C 1 -C 6 -alkyl group
  • R5, R6, R7, R8 each represent a hydrogen atom.
  • an agent according to the invention is characterized in that it contains (a) at least one substantive dye of the general formula (I) in which
  • R 1, R 4 independently of one another represent a methyl group or an ethyl group
  • R 2, R 3 independently of one another represent a hydrogen atom, a methyl group or an ethyl group
  • R5, R6, R7, R8 each represent a hydrogen atom.
  • the dyes of the formula (I) according to the invention are dimeric azo dyes which are positively charged twice.
  • the two positive charges are neutralized by the anionic counterions X1 and X2.
  • the dikationische organic part is responsible for the blue coloration of the keratin fibers.
  • the counterions X1 and X2 serve only to maintain electroneutrality, so that the exact nature of the counterions X1 and X2 does not play a significant role in achieving the desired color result. Since the dye is used in a cosmetic agent, the counterions X1 and X2 must be physiologically compatible. Physiologically acceptable in this context means suitable for use in cosmetics (ie for use on human hair and human skin).
  • X1 and X2 are physiologically acceptable anions, preferably from the group chloride, bromide, iodide, methylsulfate, methylsulfonate, p-toluenesulfonate, acetate, hydrogensulfate, V 2 sulfate and V 2 tetrachlorozincate.
  • chloride is meant an anion Ch.
  • bromide is meant an anion Br.
  • iodide is meant an anion J-.
  • methylsulfate is meant an anion H3COSO4 " .
  • an anion is "understood.
  • H3C C6H4
  • S03 is" H3CSO3 understood.
  • acetate is meant an anion H3CCOO-.
  • Hydrogen sulfate is an anion HSC - understood.
  • Below V 2 sulfate half an equivalent of the doubly negatively charged anion is SO4 understood 2 ".
  • Vi tetrachlorozincate half an equivalent of the doubly negatively charged anion ZnCU 2- understood.
  • the group Q is a grouping which links the two singly positively charged chromophores of the dye to the dicationic dimer.
  • Q is a group of the formula (II), (III), (IV) or (V),
  • n is an integer from 3 to 6
  • n, p, q each independently represent the numbers 2 or 3
  • R9 represents a hydrogen atom, a Ci-C6-alkyl group, a C2-C6-
  • Alkenyl group or a hydroxy-C 2 -C 6 -alkyl group Alkenyl group or a hydroxy-C 2 -C 6 -alkyl group.
  • the two positions marked with an asterisk in each case represent the linking positions to the two N atoms of the formula (I).
  • the linking group Q which links the two azo chromophores together, has a chain length of at least 3 atoms.
  • n in the formula (II) is an integer of at least 3.
  • the linking group Q of the formula (II) comprises at least 3 carbon atoms (ie, it is a group having the minimum length of -CH2 -CH2-CH2-).
  • m and p are each an integer of at least 2, so that this linking grouping has in total a chain length of at least 5 C and O atoms (ie, this is a group having the minimum length of -CH 2 -CH 2 -O-CH 2 -CH 2 -).
  • m, p and q are each an integer of at least 2, so that this linking grouping in an analogous manner a chain length of at least 8 C and O atoms (ie, it is a moiety with the minimum length of -CH 2 -CH 2 -O-CH 2 -
  • m and p are integers of at least 2, so that this linking group has a chain length of at least 5 C and N atoms.
  • dimeric azo dyes of the basic type of the formula (I) which, however, a non-inventive linker group Q with a
  • an agent according to the invention is characterized in that it contains (a) at least one substantive dye of the general formula (I) in which Q is a group of the formula (II),
  • n is an integer from 3 to 6.
  • an agent according to the invention is characterized in that it contains (a) at least one dye of the general formula (I) in which
  • n stands for the number 3.
  • an agent for coloring keratinic fibers is characterized in that it contains at least one compound of the general formula (I) which is selected from
  • the aforementioned compounds are dicationic dimer dyes wherein the organic dication is neutralized by the two anions X1 and X2.
  • the anions X1 - and X2 may each be a physiologically ve Nursinges anion, preferably from the group of chloride, bromide, iodide, methyl sulfate, methyl sulfonate, p-toluenesulfonate, acetate, hydrogen sulfate, Vi sulfate or Vi tetrachlorozincate.
  • an agent for dyeing keratinic fibers according to the invention is characterized in that it contains as the dye of the formula (a) at least one compound which is selected from the group consisting of 3-methyl-2- [2- (4 - ⁇ [3 - ( ⁇ 4- [2- (3-methyl-1, 3-thiazol-3-ium-2-yl) diazen-1 ⁇ yl] phenyl ⁇ amino) propyl] amino ⁇ phenyl) diazen-1-yl] -1,3-thiazole-3-ium dichloride
  • R 1, R 4 independently of one another represent a methyl group or an ethyl group
  • R 2, R 3, independently of one another, stand for a methyl group or for an ethyl group
  • R5, R6, R7 each represent a hydrogen atom
  • n stands for the number 3 or 4.
  • agents according to the invention for dyeing keratinic fibers which contain at least one dye (a) of the formula (I) which is selected from the group consisting of
  • compositions according to the invention for dyeing keratinic fibers preferably contain the substantive dye or dyes of the formula (I) in a total amount of from 0.01 to 4.5% by weight, preferably from 0.05 to 2.8% by weight, more preferably from 0.1 to 2.2 wt .-% and particularly preferably from 0.2 to 1, 2 wt .-%.
  • the amount by weight in this case refers to the total amount of all compounds of the formula (I) contained in the middle, which is related to the total weight of the agent in relation.
  • an agent according to the invention for dyeing keratinic fibers is therefore characterized in that it contains, based on the total weight of the agent, one or more substantive dyes (a) of the formula (I) in a total amount of 0.01 to 4 , 5 wt .-%, preferably from 0.05 to 2.8 wt .-%, more preferably from 0.1 to 2.2 wt .-% and particularly preferably from 0.2 to 1, 2 wt .-% contains.
  • the dyes of the general formula (I) can be prepared, for example, by a process as described in WO 2002/100369 A2.
  • the educt 2-aminothiazole can be converted in concentrated sulfuric acid with nitrosyl sulfuric acid into the diazonium ion:
  • the neutral dimer dye formed in the azo coupling reaction can be double quaternized with quaternizing agents.
  • the quaternization reaction is preferably carried out in a polar aprotic solvent (such as DMSO, DMF, etc.).
  • Suitable quaternizing agents are, for example, dimethyl sulfate, methyl iodide or p-toluenesulfonate.
  • the means for dyeing keratinic fibers contain at least one nonionic surfactant.
  • Surfactants are amphiphilic (bifunctional) compounds which consist of at least one hydrophobic and at least one hydrophilic moiety.
  • the hydrophobic group is preferably a hydrocarbon chain having 12-30 carbon atoms, which may be saturated or unsaturated, linear or branched. This C 12 -30 alkyl chain is particularly preferably linear.
  • the hydrophilic moiety comprises an uncharged hydrophilic headgroup which has strong dipole moments and is highly hydrated in aqueous solution.
  • Nonionic surfactants contain as hydrophilic group e.g. a polyol group, a polyalkylene glycol ether or a combination of polyol and polyglycol ether group.
  • hydrophilic group e.g. a polyol group, a polyalkylene glycol ether or a combination of polyol and polyglycol ether group.
  • Such compounds are, for example
  • Adducts of 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil Adducts of 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil
  • R 1 is -CO for a linear or branched, saturated and / or unsaturated acyl radical having 12 to 30 C atoms,
  • R2 is hydrogen or methyl
  • R3 is a linear or branched Ci-C4-alkyl radical
  • w is the numbers 1 to 20,
  • R 2 is a linear C 12 -C 30 -alkyl radical
  • G is a sugar residue with 5 or 6 carbon atoms, preferably glucose, and
  • p is an integer from 1 to 10, preferably an integer from 1 to 6.
  • Fatty alcohols are explicitly not nonionic surfactants in the context of the present invention.
  • Fatty alcohols in the context of the present invention fall into the group of fatty substances.
  • Dye of the formula (I) and (b) contained at least one nonionic surfactant, led to intense
  • an agent according to the invention is therefore characterized in that it contains (b) at least one nonionic surfactant selected from among
  • the adducts of 2 to 100 moles of ethylene oxide with linear and branched fatty alcohols containing 12 to 30 carbon atoms mean that each mole of fatty alcohol has been reacted with from 2 to 100 moles of ethylene oxide.
  • R 10 is a linear or branched C 12 -C 30 -alkyl group
  • x is an integer from 2 to 100.
  • R1 1 represents a linear or branched Cii-C29 alkyl group
  • y is an integer from 2 to 100
  • an agent according to the invention is therefore characterized in that it comprises as nonionic surfactant (b) at least one compound of the formula (B1) and / or at least one compound of the formula (B2) (B1)
  • R 10 is a linear or branched C 12 -C 30 -alkyl group
  • x is an integer from 2 to 100
  • R1 1 represents a linear or branched Cii-C29 alkyl group
  • y is an integer from 2 to 100
  • nonionic surfactant (b) used was a compound of the formula (B1) in which x is an integer from 10 to 50.
  • an agent according to the invention is therefore characterized in that it comprises as nonionic surfactant (b) at least one compound of the formula (B1),
  • R 10 is a linear or branched C 12 -C 30 -alkyl group
  • x is an integer from 10 to 50.
  • Particularly preferred surfactants of this embodiment are, for example, under the INCI name - Ceteareth-12 (C16 / C18 fatty alcohols, ethoxylated with 12 EO) Ceteareth-20 (C16 / C18 fatty alcohols, ethoxylated with 20 EO)
  • Ceteareth-30 (C16 / C18 fatty alcohols, ethoxylated with 30 EO)
  • the agents according to the invention for dyeing keratinic fibers preferably contain one or more nonionic surfactants (b) in a total amount of from 0.2 to 10.5% by weight, preferably from 1.0 to 7.5% by weight, more preferably from 2.0 to 4.5 wt .-% and most preferably from 2.5 to 4.5 wt .-%.
  • the data in% by weight are based on the total amount of all nonionic surfactants (b) which are related to the total amount of the colorant.
  • an agent for dyeing keratinic fibers according to the invention is therefore characterized in that it contains, based on the total weight of the composition, one or more nonionic surfactants (b) in a total amount of from 0.2 to 10.5% by weight. %, preferably from 1, 0 to 7.5 wt .-%, more preferably from 2.0 to 4.5 wt .-% and most preferably from 2.5 to 4.5 wt .-%.
  • compositions according to the invention may also contain one or more cationic surfactants.
  • Cationic surfactants are understood to mean surfactants, ie surface-active compounds, each having one or more positive charges. Cationic surfactants contain only positive charges. Usually, these surfactants are composed of a hydrophobic part and a hydrophilic head group, wherein the hydrophobic part usually consists of a hydrocarbon skeleton (eg consisting of one or two linear or branched alkyl chains), and the positive charge (s) are located in the hydrophilic head group. Cationic surfactants adsorb to interfaces and aggregate in aqueous solution above the critical micelle concentration to positively charged micelles.
  • Quaternary ammonium compounds which can carry as hydrophobic radicals one or two alkyl chains with a chain length of 8 to 28 carbon atoms
  • quaternary phosphonium salts substituted with one or more alkyl chains having a chain length of 8 to 28 C atoms or
  • the cationic charge may also be in the form of an onium structure as part of a heterocyclic ring (e.g., an imidazolium ring or a pyridinium ring).
  • the cationic surfactant may also contain other uncharged functional groups, such as is the case with esterquats.
  • Suitable cationic surfactants of this type are, for example, physiologically tolerable salts of N, N, N-trimethyl-1-hexadecanaminium, in particular N, N, N-trimethyl-1-hexadecanaminium chloride, which is also sold under the trade name Dehyquart A-CA.
  • Another suitable cationic surfactant is a physiologically acceptable salt of dimethyl distearyldimethylammonium, more preferably dimethyl distearylammonium chloride.
  • cationic surfactants can be selected from the group of cationic imidazolium compounds.
  • composition according to the invention may contain the cationic surfactant (s) in a total amount of from 0.1 to 4.8% by weight, preferably from 0.2 to 2.4% by weight, more preferably from 0.3 to 1.8 Wt .-% - based on the total weight of the composition - included.
  • Agents suitable according to the invention can furthermore be characterized in that they additionally comprise at least one zwitterionic surfactant.
  • Suitable zwitterionic surfactants are betaines, N-alkyl-N, N-dimethylammonium glycinates, N-acylaminopropyl-N, N-dimethylammonium glycinates, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines.
  • a preferred zwitterionic surfactant is known by the INCI name Cocamidopropyl Betaine.
  • Agents suitable according to the invention are characterized in that the agent additionally contains at least one amphoteric surfactant.
  • Preferred amphoteric surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids.
  • Particularly preferred amphoteric surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 -C 18 -acylsarcosine.
  • the agents according to the invention additionally comprise at least one further substantive dye in addition to the compound of the formula (I).
  • the achievable range of nuances can be extended, and the dyeing properties can be further improved.
  • Direct dyes can be subdivided into anionic, cationic and nonionic substantive dyes.
  • the substantive dyes are preferably selected from the cationic substantive dyes, since these are well compatible with the dyes of general formula (I).
  • an agent according to the invention is characterized in that it additionally contains at least one further cationic substantive dye which is different from the dyes of the formula (I).
  • Cationic dyes are understood in this context to be dyes which carry at least one positive charge.
  • One or more dyes from the group Basic Yellow 87, Basic Orange 31, Basic Red 51, Basic Violet 2 and Cationic Blue 347 have proven to be particularly compatible.
  • the dyes of the formula (I) with the cationic azo dyes Basic Orange 31 and Basic Red 51 are particularly well compatible. By combining a dye of the formula (I) with Basic Orange 31 and / or Basice Red 51 can - except pure yellow nuances - nuances in the entire color spectrum are generated.
  • an agent according to the invention is characterized in that it additionally contains Basic Orange 31 and / or Basic Red 51.
  • composition according to the invention may additionally contain at least one nonionic substantive dye.
  • This can be selected from the group HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, HC Orange 1, Disperse Orange 3, HC Red 1, HC Red 3, HC Red 7, HC Red 10 , HC Red 1 1, HC Red 13, HC Red BN, HC Blue 2, HC Blue 11, HC Blue 12, Disperse Blue 3, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, 1, 4- Diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis (2-hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- (2-hydroxyethyl) aminophenol, 2- 2-hydroxyethyl) amino-4,6-dinitrophenol, 4 - [(2-hydroxyethyl) amino] -3-nitro-1-methylbenzene, 1-amino-4- (2-hydroxyethyl) amino-5-chloro-2 nitrobenzene, 4-amino
  • anionic direct dyes may also be present, which are available under the international names or trade names Acid Yellow 1, Yellow 10, Acid Yellow 23, Acid Yellow 36, Acid Orange 7, Acid Red 33, Acid Red 52, Pigment Red 57: 1, Acid Blue 7, Acid Green 50, Acid Violet 43, Acid Black 1, Acid Black 52, Bromophenol Blue and Tetrabromophenol Blue are known.
  • the agents according to the invention can furthermore also be used together with oxidation dyes.
  • Such oxidation colorants additionally contain at least one oxidation dye precursor, preferably at least one developer-type oxidation dye precursor and at least one coupler-type oxidation dye precursor.
  • developer-type oxidation dye precursors are selected from at least one compound from the group formed from p-phenylenediamine, p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, 2- (1,2-dihydroxyethyl ) -p-phenylenediamine, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1H -imidazol-1-yl) propyl] amine, N, N'-bis (2-hydroxyethyl) -N, N'-bis (4-aminophenyl) -1, 3-diamino-propan-2-ol, bis - (2-hydroxy-5-aminophenyl) methane, 1, 3-bis (2,5-diaminophenoxy) propan-2-o
  • coupler-type oxidation dye precursors are selected from the group formed from 3-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 5 Amino-4-chloro-2-methylphenol, 5- (2-hydroxyethyl) amino-2-methylphenol, 2,4-dichloro-3-aminophenol, 2-aminophenol, 3-phenylenediamine, 2- (2,4-diaminophenoxy ) ethanol, 1, 3-bis (2,4-diaminophenoxy) propane, 1-methoxy-2-amino-4- (2-hydroxyethylamino) benzene, 1, 3-bis (2,4-diaminophenyl) propane, 2, 6-Bis (2'-hydroxyethylamino) -1-methylbenzene, 2 - ( ⁇ 3 - [(2-hydroxyethyl) amino] -4-methoxy-5-methylphenyl ⁇ amino) ethanol,
  • the additional substantive dyes, developer components and coupler components are preferably used in a proportion of 0.0001 to 5.0 wt .-%, preferably 0.001 to 3.5 wt .-%, each based on the ready-to-use agent.
  • developer components and coupler components are generally used in approximately molar amounts to each other.
  • a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components in a molar ratio of 1: 0.5 to 1: 3, in particular 1: 1 to 1: 2 , can stand.
  • the agents according to the invention additionally comprise an oxidizing agent, preferably hydrogen peroxide and / or one of its solid addition products of organic or inorganic compounds.
  • hydrogen peroxide itself is used as the aqueous solution.
  • concentration of a hydrogen peroxide solution in the composition according to the invention is determined on the one hand by the legal requirements and on the other hand by the desired effect; preferably 6 to 12 wt .-% solutions are used in water.
  • preferred application-ready means of the first subject of the invention are characterized in that, based on the total weight of the ready-to-use agent, 0.5 to 20 wt .-%, preferably 1 to 12.5 wt .-%, particularly preferably 2.5 to 10 Wt .-% and in particular 3 to 6 wt .-% hydrogen peroxide, each based on the total weight of the composition.
  • an agent according to the invention is characterized in that, based on the total weight of the composition, it is 0.5 to 12.5% by weight, preferably 2.5 to 10% by weight and in particular 3 to 6 Wt .-% hydrogen peroxide.
  • the composition may further contain at least one peroxo salt.
  • Suitable peroxo salts are inorganic peroxo compounds, preferably selected from the group formed from ammonium peroxodisulfate, alkali metal peroxodisulfates, ammonium peroxomonosulfate, alkali metal peroxomonosulfates, alkali metal peroxodiphosphates and alkaline earth metal peroxides.
  • peroxodisulfates in particular ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate.
  • an agent according to the invention is characterized in that it additionally contains at least one persulfate from the group consisting of ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate.
  • the persulfates are each in an amount of 0.5 to 20 wt .-%, preferably 1 to 12.5 wt .-%, particularly preferably 2.5 to 10 wt .-% and in particular 3 to 6 wt .-%, based on the total weight of the ready-to-use agent, contained in the agent according to the invention.
  • the dyeing and / or matting agent may contain further bleaching power boosters to enhance the bleaching effect, such as, for example, tetraacetylethylenediamine (TAED), 1,5-diacetyl-2,4-dioxo-hexahydro-1,3,5-triazine (DADHT), Tetraacetylglycoluril (TAGU), N-nonanoylsuccinimide (NOSI), n-nonanoyl or isononanoyloxybenzenesulfonate (n- or i-NOBS), phthalic anhydride, triacetin, ethylene glycol diacetate and 2,5-diacetoxy-2,5-dihydrofuran and carbonate salts or bicarbonate salts in particular ammonium bicarbonate, ammonium carbonate, sodium bicarbonate, disodium carbonate, potassium bicarbonate, dipotassium carbonate and calcium carbonate, and nitrogen-containing, heterocyclic bleach booster
  • At least one SiO 2 compound such as silica or silicates, in particular water glasses, may additionally be added to the composition according to the invention.
  • the SiO 2 compounds may be preferred according to the invention, in amounts of 0.05 wt .-% to 15 wt .-%, more preferably in amounts of 0.15 wt .-% to 10 wt .-% and most preferably in Amounts of 0.2 wt .-% to 5 wt .-%, each based on the anhydrous composition according to the invention to use. The amounts given in each case the content of the SiO 2 compounds (without their water content) in the funds again.
  • the colorants may further contain additional active ingredients, auxiliaries and additives in order to improve the dyeing performance and to adjust further desired properties of the agents.
  • the colorants are provided as a liquid preparation and the agents therefore optionally additionally added a further surfactant, said surfactants depending on the field of application as surfactants or as emulsifiers: They are preferably selected from anionic, zwitterionic, amphoteric and nonionic surfactants and emulsifiers ,
  • the colorants of the invention may contain other auxiliaries and additives.
  • the agent contains at least one thickener.
  • these thickeners there are no fundamental restrictions. Both organic and purely inorganic thickening agents can be used.
  • Suitable thickeners are
  • thickeners such as nonionic guar gums, scleroglucan gums or xanthan gums, gum arabic, ghatti gum, karaya gum, gum tragacanth, carrageenan gum, agar, locust bean gum, pectins, alginates, starch fractions and derivatives such as amylose, Amylopectin and dextrins, as well as cellulose derivatives such as methylcellulose, carboxyalkylcelluloses and hydroxyalkylcelluloses;
  • nonionic guar gums such as nonionic guar gums, scleroglucan gums or xanthan gums, gum arabic, ghatti gum, karaya gum, gum tragacanth, carrageenan gum, agar, locust bean gum, pectins, alginates, starch fractions and derivatives such as amylose, Amylopectin and dextrins, as well as cellulose derivatives such
  • nonionic, fully synthetic polymers such as polyvinyl alcohol or polyvinylpyrrolidinone; as well as inorganic thickening agents, in particular phyllosilicates such as, for example, bentonite, especially smectites, such as montmorillonite or hectorite.
  • the pH of the ready-to-use agent is between 7 and 11, in particular between 8 and 10.5.
  • the pH values are pH values which were measured at a temperature of 22 ° C.
  • the alkalizing agents which can be used in accordance with the invention for adjusting the preferred pH can be selected from the group consisting of ammonia, alkanolamines, basic amino acids and inorganic alkalizing agents such as (earth) alkali metal hydroxides, (earth) alkali metal metasilicates, (alkaline) alkaline metal phosphates and (Alkaline) alkali metal hydrogen phosphates.
  • Preferred inorganic alkalizing agents are magnesium carbonate, sodium hydroxide, potassium hydroxide, sodium silicate and sodium metasilicate.
  • Organic alkalizing agents which can be used according to the invention are preferably selected from monoethanolamine, 2-amino-2-methylpropanol and triethanolamine.
  • the basic amino acids which can be used as alkalizing agents according to the invention are preferably selected from the group formed from arginine, lysine, ornithine and histidine, more preferably arginine. It has become part of the Investigations to the present invention pointed out that further preferred agents according to the invention are characterized in that they additionally contain an organic alkalizing agent.
  • An embodiment of the first subject of the invention is characterized in that the agent additionally contains at least one alkalizing agent which is selected from the group consisting of ammonia, alkanolamines and basic amino acids, in particular ammonia, monoethanolamine and arginine or its compatible salts.
  • the colorants in particular if they additionally contain hydrogen peroxide, contain at least one stabilizer or complexing agent.
  • Particularly preferred stabilizers are phenacetin, alkali benzoates (sodium benzoate) and salicylic acid.
  • all complexing agents of the prior art can be used.
  • Preferred complexing agents according to the invention are nitrogen-containing polycarboxylic acids, in particular EDTA and EDDS, and phosphonates, in particular 1-hydroxyethane-1,1-diphosphonate (HEDP) and / or ethylenediaminetetramethylenephosphonate (EDTMP) and / or diethylenetriaminepentamethylenephosphonate (DTPMP) or their sodium salts.
  • HEDP 1-hydroxyethane-1,1-diphosphonate
  • EDTMP ethylenediaminetetramethylenephosphonate
  • DTPMP diethylenetriaminepentamethylenephosphonate
  • the agents according to the invention may contain further active ingredients, auxiliaries and additives, for example nonionic polymers such as, for example, vinylpyrrolidinone / vinyl acrylate copolymers, polyvinylpyrrolidinone, vinylpyrrolidinone / vinyl acetate copolymers, polyethylene glycols and polysiloxanes; additional silicones, such as volatile or nonvolatile, straight-chain, branched or cyclic, crosslinked or uncrosslinked polyalkylsiloxanes (such as dimethicones or cyclomethicones), polyarylsiloxanes and / or polyalkylarylsiloxanes, in particular polysiloxanes with organofunctional groups, such as substituted or unsubstituted amines (amodimethicones), carboxyl, Alkoxy and / or hydroxyl groups (dimethicone copolyols), linear polysiloxane (A) polyoxyalkylene (B) block copo
  • the choice of these other substances will be made by those skilled in the art according to the desired properties of the agents. With regard to further optional components and the amounts of these components used, reference is expressly made to the relevant manuals known to the person skilled in the art.
  • the additional active ingredients and auxiliaries are preferably used in the agents according to the invention in amounts of from 0.0001 to 25% by weight, in particular from 0.0005 to 15% by weight, based on the total weight of the application mixture.
  • keratinic fibers can be dyed in extremely attractive and intense shades of blue.
  • the dyes of the general formula (I) are cationic dimeric azo dyes. It has surprisingly been found that the color intensity of cationic azo dyes can be increased even further by addition of one or more nonionic surfactants (b) of the formula (B1),
  • R 10 is a linear or branched C 12 -C 30 -alkyl group
  • x is an integer from 2 to 100.
  • a second subject of the present invention is therefore the use of one or more nonionic surfactants (b) of the formula (B1)
  • R 10 is a linear or branched C 12 -C 30 -alkyl group and x is an integer from 2 to 100.
  • the improvement of the color absorption capacity is understood to mean that the dyes increasingly diffuse into the keratinic fiber, which leads to dyeings having a higher color intensity.
  • the intensified color intensity can be detected either visually by viewing under a daylight lamp or by colorimetric measurement (determination of the Lab values).
  • Geeigente cationic azo dyes are, for example, the dyes Basic Yellow, Basic Orange 31 and Basic Red 51.
  • a further subject of the present invention is therefore the use of one or more nonionic surfactants (b) of the formula (B1)
  • R 10 is a linear or branched C 12 -C 30 -alkyl group
  • x is an integer from 2 to 100.
  • the agents according to the invention can be formulated as single-component agents or as multicomponent agents, such as two-component agents or three-component agents, and used accordingly. Separation into multicomponent systems is particularly suitable where incompatibilities of the ingredients are to be expected or feared; the agent to be used in such systems is manufactured by the consumer just prior to use by mixing the component.
  • the agent according to the invention for the color change of keratinic fibers is always understood to mean the ready-to-use agent.
  • the agent according to the invention is made available to the user in the form of a one-component agent, then the ready-to-use agent does not first have to be prepared, but can be produced directly The container in which it was made, be removed and applied to the keratinic fibers.
  • Bleaching agents are usually two-component products in which an oxidizing agent-containing component (A1) shortly before application with an (alkalizing) agent
  • the agent according to the invention is the ready-to-use agent which was prepared shortly before use by mixing (A1) and (A2).
  • Alkalizing agent are made up.
  • the nonionic surfactant (s) may also be used in the
  • Component (A1) i.e., together with the oxidizing agent
  • component (A2) i.e., a oxidizing agent
  • the ready-to-use agent is prepared by mixing three components shortly before application to the human hair
  • the component (A1) at least one substantive dye of the general formula (I) and at least one alkalizing agent
  • Component (A2) contains at least one first oxidizing agent (for example hydrogen peroxide) and
  • Component (A3) contains at least one second oxidizing agent (e.g., one or more poroxodisulfate salts).
  • At least one of the components (A1), (A2) and (A3) again contains at least one nonionic surfactant (b).
  • the heat input may be provided by an external heat source, e.g. warm air of a hot air blower, as well as, especially in a hair whitening on living subjects, done by the body temperature of the subject. In the latter case, the treated batch is usually covered with a hood.
  • An exposure phase at room temperature is also according to the invention. In particular, the temperature during the exposure time between 20 ° C and 40 ° C, in particular between 25 ° C and 38 ° C.
  • the remaining dyeing preparation is rinsed with water or a cleaning agent from the hair.
  • a cleaning agent can be used in particular commercial shampoo, in particular then can be dispensed with the detergent and the rinsing can be done with water when the brightening agent has a strong surfactant-containing carrier.
  • the dye DZ 1 was synthesized by a process as described in documents WO 2002/100369 A2 and US 3291788.
  • 2-aminothiazole and N, N'-dimethyl-N, N'-diphenyl-ethane-1, 2-diamine were used (azo coupling reaction in aqueous, sulfuric acid solution with nitrosyl sulfuric acid).
  • the dye resulting from this azo coupling reaction was then quaternized (for example, with a quaternizing agent such as dimethyl sulfate in a polar, aprotic solvent such as dimethylformamide or dimethylsulfoxide).
  • the fatty alcohols (fats) were melted together with the parabens. This melt was emulsified with the particular surfactants used and hot water, then the pre-dissolved in propylene glycol dye was added and the ammonium sulfate solution was added. The indicated pH was adjusted with ammonia, then made up to 100 g with water. colorations
  • Each 1, 8 g of the dyeing cream were applied to an approximately 6 cm long strand of human hair (Kerling Euronaturhaar, 80% gray) and left there for 30 minutes at 30 ° C. After completion of the exposure time, the hair was rinsed, washed with a conventional shampoo and then dried. After drying, the color and intensity of the streaks were visually evaluated under the daylight lamp.
  • the formulations V1 and V2 are comparative formulations which contain the substantive dye DZ 2 which is not according to the invention (DZ 2: 3-methyl-2- (2- ⁇ 4- [methyl (2-methyl [4-] 2- (3-methyl-1,3-thiazol-3-ium-2-yl) diazen-1-yl] phenyl ⁇ ) amino] ethyl ⁇ ) amino] phenyl ⁇ diazen-1-yl) -1, 3 thiazole-3-di (methylsulfate) (comparative)).
  • DZ 2 3-methyl-2- (2- ⁇ 4- [methyl (2-methyl [4-] 2- (3-methyl-1,3-thiazol-3-ium-2-yl) diazen-1-yl] phenyl ⁇ ) amino] ethyl ⁇ ) amino] phenyl ⁇ diazen-1-yl) -1, 3 thiazole-3-di (methylsulfate) (comparative)).
  • Formulation V3 is a comparative formulation which, although containing a substantive dye of general formula (I), but instead of a nonionic surfactant, the zwitterionic surfactant cocoamidopropyl betaine (alternative name: ⁇ [3- (dodecanoylamino) propyl] - (dimethyl) ammonio ⁇ acetate), CAS no. 61789-40-0).
  • cocoamidopropyl betaine alternative name: ⁇ [3- (dodecanoylamino) propyl] - (dimethyl) ammonio ⁇ acetate
  • the hair strand was dyed dark purple with this formulation.
  • the formulation E1 was a formulation according to the invention which contained the substantive dye DZ1 according to the invention in combination with nonionic surfactants.
  • DZ1 3-methyl-2- (2- ⁇ 4- [methyl ( ⁇ 3- [methyl ( ⁇ 4- [2- (3-methyl-1,3-thiazol-3-ium-2-yl) -diazene 1 -ylphenyl ⁇ ) -amino] propyl ⁇ ) amino] phenyl ⁇ diazen-1-yl) -1,3-thiazol-3-ium, di (methylsulfate)). It was an intense, deep dark blue, almost black color without red content obtained.

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Abstract

La présente invention concerne des agents de coloration de fibres kératiniques, notamment de cheveux humains, contenant dans un excipient cosmétique : (a) au moins un colorant direct de formule (I), et (b) au moins un tensioactif non ionique.
PCT/EP2015/072774 2014-11-25 2015-10-02 Agents de coloration de fibres kératiniques, contenant au moins un colorant azoïque dicationique dimère et au moins un tensioactif non ionique WO2016082999A1 (fr)

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EP15771640.8A EP3223787B1 (fr) 2014-11-25 2015-10-02 Agents de coloration de fibres kératiniques, contenant au moins un colorant azoïque dicationique dimère et au moins un tensioactif non ionique
US15/528,539 US10226648B2 (en) 2014-11-25 2015-10-02 Agents for dyeing keratin fibres, containing at least one dimeric, dicationic azo dye and at least one non-ionic surfactant

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DE102014223938.9A DE102014223938A1 (de) 2014-11-25 2014-11-25 Mittel zum Färben von keratinischen Fasern, enthaltend mindestens einen dimeren, dikationischen Azofarbstoff und mindestens ein nichtionisches Tensid

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EP3223787B1 (fr) 2019-09-11

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